Derivatives of propionic acid



atented 1 1946 r 483 grams of the benzyloxypropionitrile, 600 cc. of i Nrnzp STATES PATENT. OFFICE DERIVATIVES F PROPIONIC ACID Albert M. Clifford and Joy G. Lichty, Stow, Ohio,

assignors to Wingfoot Corporation, Wilmington, Del., a corporation of Delaware No Drawing. Application February 10, 1943, Serial No. 475,428

1 Claim. (Cl. 260-473) This invention relates to esters which have been trile, 180 grams Cellosolve (hydroxyethyl ether), found satisfactory as plasticizers for polyvinyl and 18 grams water at a temperature of about alcohol, polyvinyl butyraldehyde, copolymers of 90 C until no more ammonium hl i gpvlnyl hlori and vi ylill n chloride, 1 3 arated. Distillation of the filtrate gave a good mers of butadiene and acrylonitrile, etc. The 5 yield of the ester boning 1904000 (H35 compounds are esters of aralkoxypropionic acid The amount of water used may be reduced or and have the formula? the conversion of the nitriie to the ester may be R.O- H2- R" R' carried out with alcohol in the absence of water. where Ris aralkyl, R is alkyl, aralkyl or alicyclic, to Oth in a ds, s h as sulfu i acid. may and R" is hydrogen, methyl or ethyl. replace the HCl. l

The invention will be illustrated by the follow- Other compounds having the above general foring examples: .miila which may be prepared in a man- EXAMPLE 1 nor are: Amyl-beta-benzylomypropionate Cyclohexyl-fl-benzyloxypropionate CaHsCH20.C2H4.COOC51-Iu o tyl-p-benzyloxy mpionate Beta-benzyloxypropionitrile was prepared by Dfl yl-flzy1 xyp p e the addition of benzyl alcohol to acrylonitrile with Butyl-fl-benxyloxy-o-methyl-propionate sodium methylate as a catalyst. A mixture of Cyclohexyl-p-benzyloxy-o-ethylpropionate Ethyl-p-phenylethoxy propionate mixed amyl alcohols, and 54 grams of water was Methyla-(p-methoxybenzyloxy) propionate heated to 90 C. on a steam bath. Dry HCl, gas' was bubbled into the solution until little addi- What we claim i i tional ammonium chloride separated. 'The liquid Amyl-beta-benzyloxypr p n te. h D h e :1 Y1 portion of the reaction on distillation gave a. good group of which is linked to the oxy group through yield of an ester boiling at l90220 C./ mm.- the methylene group of the benzyl radical.

2 r Amm'r M CLIFFORD Ethoxyethyl beta-benzylozyproplonate a0 JOY G.

CsHsCHaOCaHa COO.C2H4.0C2I-Is This compound was prepared by adding gaseous H01 to a mixture or 161 grams benzyloxypropioni- 

